Substituted 2H-pyran-2,6(3H)-dione derivatives

Abstract

Substituted 2H-pyran-2,6(3H)-dione derivatives useful in the treatment of allergic conditions are prepared by reaction of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one with an appropriate aniline.

What is claimed is: 
     
       1. A compound represented by the formula: ##STR11## wherein: R 1  represents --NHCOCH 2  CH 2  COOR 3 , --NHCOCOCOOH or ##STR12## R 2  represents hydrogen or, when R 1  is ##STR13##  also represents amino or ##STR14##  and R 3  represents lower alkyl having one or two carbon atoms; or a mono- or di-alkali metal salt of said compound. 
     
     
       2. A compound according to claim 1 in which R 1  is in the 3-position. 
     
     
       3. A compound according to claim 2 in which R 2  is hydrogen. 
     
     
       4. A compound according to claim 3 in which R 1  is methylsuccinoylamino. 
     
     
       5. A compound according to claim 3 in which R 1  is ketomalonoylamino. 
     
     
       6. A compound according to claim 3 in which R 1  is glyceroylamino. 
     
     
       7. A compound according to claim 2 in which R 1  is glyceroylamino and R 2  is amino. 
     
     
       8. A compound according to claim 2 in which R 1  and R 2  are glyceroylamino. 
     
     
       9. A pharmaceutical composition for inhibiting the symptoms of asthma comprising a nontoxic pharmaceutical carrier or diluent and an amount sufficient to produce said inhibition of a compound represented by the formula: ##STR15## wherein: R 1  represents --NHCOCH 2  CH 2  COOR 3 , --NHCOCOCOOH or ##STR16## R 2  represents hydrogen or, when R 1  is ##STR17##  also represents amino or ##STR18##  and R 3  represents lower alkyl having one or two carbon atoms; or a mono- or di-alkali metal salt of said compound. 
     
     
       10. A pharmaceutical composition according to claim 9 in a form suitable for administration by inhalation. 
     
     
       11. A pharmaceutical composition according to claim 9 comprising a solution or suspension of the active ingredient in sterile water. 
     
     
       12. A pharmaceutical composition according to claim 9 in the form of an aerosol formulation. 
     
     
       13. A pharmaceutical composition according to claim 9 in which the pharmaceutical carrier or diluent is a solid. 
     
     
       14. A pharmaceutical composition according to claim 9 in which R 1  is 3-methylsuccinoylamino. 
     
     
       15. A pharmaceutical composition according to claim 9 in which R 1  is 3-ketomalonoylamino. 
     
     
       16. A pharmaceutical composition according to claim 9 in which R 1  is 3-glyceroylamino and R 2  is hydrogen. 
     
     
       17. A pharmaceutical composition according to claim 9 in which R 1  is 3-glyceroylamino and R 2  is amino. 
     
     
       18. A pharmaceutical composition according to claim 9 in which R 1  is 3-glyceroylamino and R 2  is glyceroylamino. 
     
     
       19. A pharmaceutical composition according to claim 9 in dosage unit form and in which the active ingredient is in an amount of from about 0.5 mg. to about 500 mg. per dosage unit. 
     
     
       20. A method of inhibiting the symptoms of asthma which comprises administering to an animal in need of said inhibition a therapeutically effective amount for producing said inhibition of a compound represented by the formula: ##STR19## wherein: R 1  represents --NHCOCH 2  CH 2  COOR 3 , --NHCOCOCOOH or ##STR20## R 2  represents hydrogen or, when R 1  is ##STR21##  also represents amino or ##STR22##  and R 3  represents lower alkyl having one or two carbon atoms; or a mono- or di-alkali metal salt of said compound. 
     
     
       21. The method according to claim 20 in which the active ingredient is administered in a daily dosage regimen of from about 0.5 mg. to about 2000 mg.